Propylene → Methyl 2-chloro-(5-methyl-4,5-dihydroisoxazol-3-yl)-4-methylsulfonylbenzoate

HRID 1276116Notes

Reaction equation

HRID 1276116 reaction equation
[CH2:1]=[CH:2][CH3:3].[Cl:4][C:5]1[C:14]([CH:15]=[N:16][OH:17])=[C:13]([S:18]([CH3:21])(=[O:20])=[O:19])[CH:12]=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8].C([O-])(=O)C.[Na+].Cl[O-].[Na+]>ClCCl>[Cl:4][C:5]1[C:14]([C:15]2[CH2:1][CH:2]([CH3:3])[O:17][N:16]=2)=[C:13]([S:18]([CH3:21])(=[O:20])=[O:19])[CH:12]=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8]

Participants

6

Reactant 4

HCID 8252Propylene4×HCID 517045Sodium AcetateHCID 23665760Sodium HypochloriteHCID 86584467Methyl 2-chloro-3-hydroxyiminomethyl-4-methylsulfonylbenzoate

Product 1

HCID 22114913Methyl 2-chloro-(5-methyl-4,5-dihydroisoxazol-3-yl)-4-methylsulfonylbenzoateYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

At room temperature, propene was introduced into a solution of 15.0 g (52 mmol) of methyl 2-chloro-3-hydroxyiminomethyl-4-methylsulfonylbenzoate and 200 ml of dichloromethane for 30 minutes. After the addition of 1.6 g of sodium acetate, 42.8 ml of sodium hypochlorite solution were added dropwise, with the simultaneous introduction of propene. At room temperature, propene was subsequently introduced into the mixture for a further 15 minutes. The mixture was heated for 3 hours under reflux and then stirred for 12 hours at room temperature, propene was introduced once more under reflux for 5 hours and the mixture was stirred at room temperature for another 12 hours. The phases were separated and the organic phase was washed with water, dried and concentrated. 15.5 g (89% of theory) of methyl 2-chloro-(5-methyl-4,5-dihydroisoxazol-3-yl)-4-methylsulfonylbenzoate were obtained.

Workup

  1. temperatureThe mixture was heated for 3 hours
  2. temperatureunder reflux
  3. temperatureunder reflux for 5 hours
  4. stirringthe mixture was stirred at room temperature for another 12 hours
  5. customThe phases were separated
  6. washthe organic phase was washed with water
  7. customdried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-dd852644eccc4a558ff583d8ed0222b2
Source dataset
uspto-grants-2000_12
Patent number
US06165944

Reaction notes

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